Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane丨cas 126726-62-3 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Bulk Inquiry 4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane丨CAS 126726-62-3
4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (CAS 126726-62-3), also known as isopropenylboronic acid pinacol ester or 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, is an organoboron compound containing an isopropenyl group attached to a pinacol boronate ester. Its structure combines a reactive carbon–carbon double bond with a boronate ester functionality, making it a versatile building block for organic synthesis, pharmaceutical intermediate development, medicinal chemistry, and functional materials research.
Chemical Identifiers
| InChI | 1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3 |
| InChI Key | SVSUYEJKNSMKKW-UHFFFAOYSA-N |
| Smiles | C=C(B1OC(C)(C)C(C)(C)O1)C |
| EC No. | 627-007-7 |
| MDL No. | MFCD08276843 |
| PubChem CID | 10997426 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
This compound is a useful coupling partner in Suzuki–Miyaura reactions for introducing an isopropenyl group into aromatic and heteroaromatic structures. Under suitable palladium-catalyzed conditions, the boronate ester functionality participates in carbon–carbon bond formation with compatible organic halides. The resulting products contain an alkene group that can undergo further chemical transformations, providing a convenient route to functionalized organic intermediates.
Applications in Pharmaceutical Intermediate Synthesis
4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane serves as a building block for preparing alkene-containing pharmaceutical intermediates. Its isopropenyl functionality enables the introduction of a three-carbon fragment into selected molecular frameworks. The resulting compounds may undergo hydrogenation, oxidation, or other suitable transformations, supporting multistep synthesis and the development of structurally diverse pharmaceutical research compounds.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound provides a route for introducing a substituted vinyl group into candidate molecules. The isopropenyl fragment can influence molecular geometry, hydrophobicity, and subsequent synthetic reactivity. Researchers may use the compound in analog synthesis, lead optimization, and structure–activity relationship studies to investigate the effects of alkene substitution on molecular properties.
Applications in Functionalized Biaryl Synthesis
The compound is particularly useful for preparing substituted alkenes through carbon–carbon cross-coupling reactions. Its boronate ester group allows the transfer of the isopropenyl fragment to compatible coupling partners, producing terminal methylene-containing structures of the general form R–C(CH₃)=CH₂. These products can serve as intermediates for further functionalization, including hydrogenation, epoxidation, and selected oxidation reactions.
